tert-Butyl β-D-galactopyranoside | 36793-04-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-Butyl β-D-galactopyranoside
• 英文别名: (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(2-methylpropan-2-yl)oxy]oxane-3,4,5-triol
• CAS: 36793-04-1
• 化学式: C₁₀H₂₀O₆
• 分子量: 236.265
• InChiKey: FYTBMEIHHNSHKR-NXRLNHOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-Butyl β-D-galactopyranoside 在 sodium hydride 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (4aR,6S,7R,8S,8aS)-7,8-Bis-benzyloxy-6-tert-butoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine
  参考文献：
  名称：

  Synthesis of rhamnogalacturonan I oligosaccharides: synthesis of a tetrasaccharide intermediate

  摘要：

  A hydroxyl protected tetrasaccharide intermediate, corresponding to a segment of the rhamnogalacturonan I polysaccharide, has been synthesized using the glycosyl imidate technique. This tetrasaccharide is designed to allow for further elongation and branching. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00494-7
• 作为产物：
  描述：

  tert-butyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 Amberlyst A-26(OH) 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以94%的产率得到tert-Butyl β-D-galactopyranoside
  参考文献：
  名称：

  糖与强碱离子交换树脂的催化脱酰作用；Zemplén程序的替代方法

  摘要：

  强碱离子交换树脂可用于糖的催化脱酰反应。这项新技术可轻松分离水溶性产品而无需去离子。

  DOI：

  10.1039/c39810000760

文献信息

• GLYCOSIDE COMPOUND AND PREPARATION METHOD THEREFOR, COMPOSITION, APPLICATION, AND INTERMEDIATE
  申请人：SHANGHAI HUTCHISON PHARMACEUTICALS LIMITED

  公开号：US20210115082A1

  公开（公告）日：2021-04-22

  The present invention discloses a glycoside compound represented by Formula III, and a preparation method, a composition, use and an intermediate thereof. The glycoside compound provided in the present invention has simple preparation method, can significantly increase the expression of VEGF-A mRNA, and is effective in promoting the angiogenesis. This provides a reliable guarantee for the development of drugs with pro-angiogenic activity for treating cerebral infarction cerebral stroke, myocardial infarction, and ischemic microcirculatory disturbance of lower limbs.

  本发明公开了一种由III式表示的糖苷化合物，以及其制备方法、组合物、用途和中间体。本发明提供的糖苷化合物具有简单的制备方法，可以显著增加VEGF-A mRNA的表达，并且在促进血管生成方面具有有效性。这为开发具有促血管生成活性的药物治疗脑梗死、脑卒中、心肌梗死和下肢缺血微循环障碍提供了可靠的保证。
• A Facile Transgalactosylation catalyzed by a Lipid-Coated β-<i>D</i>-Galactosidase in the Water-Organic Two Phases
  作者：Toshiaki Mori、Sanae Fujita、Yoshio Okahata

  DOI：10.1246/cl.1997.73

  日期：1997.1

  A lipid-coated β-D-galactosidase could act as an efficient catalyst for transgalactosylation in the water-organic two phases: both the hydrophobic lipid-coated enzyme and alcohols were solubilized in isopropyl ether and mixed with an aqueous solution of lactose (a galactosyl donor). When a native β-D-galactosidase was employed for the same reaction, neither the transgalactosylation nor the hydrolysis reaction proceeded due to the deactivation of the enzyme at the interface.

  一种脂质包被的β-D-半乳糖苷酶可以作为水-有机两相中转半乳糖基化的高效催化剂：脂肪性脂质包被的酶和醇在异丙醚中被溶解，并与乳糖（半乳糖基供体）的水溶液混合。当使用天然的β-D-半乳糖苷酶进行相同反应时，由于酶在界面处失活，既未发生转半乳糖基化反应，也未发生水解反应。
• Iodine: A versatile reagent in carbohydrate chemistry II. Efficient chemospecific activation of thiomethylglycosides
  作者：K.P. Ravindranathan Kartha、Mahmoud Aloui、Robert A. Field

  DOI：10.1016/0040-4039(96)01029-5

  日期：1996.7

  Iodine has been found to be an efficient promoter in the alcoholysis of unprotected or fully benzylated methyl 1-thio-β-D-galactopyranoside. Stereoselective formation of 1,2-cis linkages in oligosaccharide synthesis using “armed” thiomethyl glycosides as glycosyl donors was also observed. Protecting groups such as acetate, benzoate, benzylidene, isopropylidene, trimethylsilylethyl etc are stable under

  已发现碘是未保护的或完全苄基化的甲基1-硫代-β - D-吡喃半乳糖苷的醇解中的有效启动子。还观察到在寡糖合成中使用“武装”的硫代甲基糖苷作为糖基供体的立体选择性形成1，2-顺式键。在反应条件下，保护基如乙酸根，苯甲酸酯基，亚苄基，亚异丙基，三甲基甲硅烷基乙基等是稳定的。
• Stereoselective protecting-group-free synthesis of alkyl glycosides using dibenzyloxy triazine type glycosyl donors
  作者：Gefei Li、Masato Noguchi、Masaki Ishihara、Yuka Takagi、Marina Nagaki、Sachie Saito、Masashi Saito、Xin-shan Ye、Shin-ichiro Shoda

  DOI：10.1016/j.carres.2023.108940

  日期：2023.12

  key step for the synthesis of sugar-containing molecules such as glycolipids. However, traditional carbohydrate chemistry is characterized by extensive use of protective groups, resulting in laborious manipulations and poor atom economy. Here, we present a protecting-group-free glycosylation strategy employing dibenzyloxy-1,3,5-triazin-2-yl glycosides (DBT-glycosides) as glycosyl donors. The DBT-glycosyl

  化学O-糖基化是合成糖脂等含糖分子的关键步骤。然而，传统的碳水化合物化学的特点是广泛使用保护基团，导致操作繁琐且原子经济性差。在这里，我们提出了一种使用二苄氧基-1,3,5-三嗪-2-基糖苷（DBT-糖苷）作为糖基供体的无保护基糖基化策略。 DBT-糖基供体可以通过水介质中未受保护的糖的碱性亲核取代直接制备。在温和的氢解条件下，使用 DBT-糖基供体对醇进行O-糖基化，以良好的产率立体选择性地提供相应的烷基糖苷。
• Glycoside compound and preparation method therefor, composition, application, and intermediate
  申请人：SHANGHAI HUTCHISON PHARMACEUTICALS LIMITED

  公开号：US11325937B2

  公开（公告）日：2022-05-10

  The present invention discloses a glycoside compound represented by Formula III, and a preparation method, a composition, use and an intermediate thereof. The glycoside compound provided in the present invention has simple preparation method, can significantly increase the expression of VEGF-A mRNA, and is effective in promoting the angiogenesis. This provides a reliable guarantee for the development of drugs with pro-angiogenic activity for treating cerebral infarction cerebral stroke, myocardial infarction, and ischemic microcirculatory disturbance of lower limbs.

  本发明公开了一种由式 III 表示的糖苷化合物及其制备方法、组合物、用途和中间体。本发明提供的苷类化合物制备方法简单，能显著提高血管内皮生长因子-A mRNA的表达，有效促进血管生成。这为开发治疗脑梗塞脑中风、心肌梗塞、下肢缺血性微循环障碍等具有促血管生成活性的药物提供了可靠保证。